Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

S. M. Biros, E. C. Ullrich, F. Hof, Laurent Alain Claude Trembleau, J. Rebek Jnr

Research output: Contribution to journalArticle

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Abstract

We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

Original languageEnglish
Pages (from-to)2870-2876
Number of pages6
JournalJournal of the American Chemical Society
Volume126
DOIs
Publication statusPublished - 2004

Keywords

  • MOLECULAR RECOGNITION
  • AQUEOUS-MEDIA
  • SYNTHETIC RECEPTORS
  • AMMONIUM CATIONS
  • CAVITANDS
  • INCLUSION
  • GUEST
  • ACETYLCHOLINE
  • CHEMOSENSOR
  • DERIVATIVES

Cite this

Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity. / Biros, S. M.; Ullrich, E. C.; Hof, F.; Trembleau, Laurent Alain Claude; Rebek Jnr, J.

In: Journal of the American Chemical Society, Vol. 126, 2004, p. 2870-2876.

Research output: Contribution to journalArticle

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T1 - Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

AU - Biros, S. M.

AU - Ullrich, E. C.

AU - Hof, F.

AU - Trembleau, Laurent Alain Claude

AU - Rebek Jnr, J.

PY - 2004

Y1 - 2004

N2 - We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

AB - We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

KW - MOLECULAR RECOGNITION

KW - AQUEOUS-MEDIA

KW - SYNTHETIC RECEPTORS

KW - AMMONIUM CATIONS

KW - CAVITANDS

KW - INCLUSION

KW - GUEST

KW - ACETYLCHOLINE

KW - CHEMOSENSOR

KW - DERIVATIVES

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

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